Lil Squeaky

Squeakarius Vercingétorix Jjezczsweckopvf Martinsburger McBride, known professionally as Lil Squeaky (also known as Shareef and formerly XXX Biggie T), is a Finnish-American rapper, singer, songwriter, record producer, politician, stripper, and pottery artist. He initially gained notoriety for his extensive discography on his original SoundCloud account, before signing to Flex Entertainment. He is best known for singles such as the "Menace" song series, "Darkness," "Tear Dat A$$ Up," "Cyberbully," '"Games," "In Bloom," "Powerball," the TikTok hit "Crocs on my Feet", and the smash hit song "Nipples." He served as a member of the Flexistan House of Representatives from Virginia's 8th congressional district from 2015 to 2021 as the sole representative from the Baller Party. He attempted to run for president in both 2020 and 2021, and has announced intentions to run in 2024. He is also seeking to reclaim his House seat in 2022.

His music contains a wide variety of production styles and vocal deliveries, with most of his music containing elements of cloud rap and trap rap, and at times experimenting with pop, rock, EDM, and R&B. He is the older brother of former Flex Entertainment artist .jitters, and the two have collaborated several times between 2018 and .jitters' retirement. He is also the older brother of professional scammer and former competitive Minecraft player Lil Nav.

He became an executive in the label on September 24, 2020, and stepped down from that position on February 23, 2021. He left Flex Entertainment on April 22, 2021. After leaving, he began to incorporate more of an "underground" sound and aesthetic to his music. He signed back to Flex Entertainment on January 11, 2022.

Early Life
Lil Squeaky was born on December 16, 2002, in Helsinki, Finland, as the second child of four. His mother is from Bangladesh, and was adopted by a wealthy Finnish couple at the age of seven. His father is a pure-blooded Finnish man. Squeaky grew up in various parts of Northern Virginia, where he recorded the majority of his discography.

Career
Lil Squeaky released his first single, “Fake Lil Squeaky,” in May 2018, a diss track towards fellow Virginia rapper Lil Crisp. He released several more singles in late spring and early summer 2018 on SoundCloud, and gained a following over the summer. He released his debut mixtape Squeakerton, The Chronicle on September 21, 2018. Just a few weeks later in October he released the EP Jews in the Ghetto, vol. 1. Then on November 3, 2018, he released the mixtape Deadass: Ricky’s Last Stand. The song “MANNY” from this mixtape became popular nearly two years later in July 2020 after being posted on the Reddit page Cringetopia. Shortly after the Deadass mixtape was released, the Lil Squeaky character “died.”  This is because Squeaky didn’t feel any motivation to make music, so he killed off the character of Lil Squeaky. However, at the end of the year, he decided to revive the character and continue making music.

On February 10, 2019, Squeaky released his most recent mixtape Jews in the Ghetto, vol. 2.  Later that month he released the double-single Spooky Hours, which featured the two lead singles for his upcoming debut album. His first studio album, Professional Murderer, was released on April 9, 2019, and was intended to be a very loud, experimental album. The album garnered mixed reviews, with many listeners enjoying the album’s absurdity and Squeaky’s brand of satire, while others criticized its length and how distorted and abrasive the album’s sound was. The album has gone on to spawn numerous sleeper hit songs, though, and has been looked back on positively by fans, with Squeaky himself calling it his best work to date. Squeaky went on hiatus after this, and released two singles in May 2019 under the moniker XXX Biggie T. The Soundcloud account he used for those songs would later become his second account for his Lil Squeaky music.

Squeaky was signed to Flex Entertainment on October 31, 2019, and released his first single under the label, “Menace,” featuring Lil Mosquito Disease and Big Lil, in November. Squeaky gained a much greater following after releasing the song, and it peaked at number 51 on the Flex Entertainment Hot 100, long after its initial release and peak popularity. Squeaky’s follow-up single “Menace 2,” featuring Lil Mosquito Disease, Big Lil, and beetlebat, was released late in November, and peaked at number 67. "Menace 2" became Squeaky's first song to reach 1,000 plays on Spotify.

In 2020, Squeaky’s first release was the single “Ok,” and shortly after announced that he was working on his second studio album Menace 2 Society. The album was intended to be a "meme rap version of Travis Scott's Rodeo album." However, he would later announce that the entire album was scrapped and he would instead attempt to make an album that people would listen to unironically in their free time while still including lyrics that could make people laugh. He does plan on eventually releasing the scrapped songs. To entertain fans before he album would be released, he released two projects: a live compilation album, Squeaky Sings the Classics, released on April 10 on SoundCloud and YouTube, and the EP Squeaky 4 President, released on SoundCloud and YouTube on April 17 and onto streaming services on April 31. The EP was met with generally positive reviews, with many listeners finding the songs catchy, though others disliked the poor mastering and the very questionable lyrics. The extended-play debuted at number ten on the Braeden's Most Played Albums chart with 100,000 album-equivalent units. The EP spawned Squeaky’s first top ten hit, “Nipples,” which peaked at number 7 on the Flex Entertainment Hot 100. Thanks to this EP and especially the success of "Nipples," Squeaky gained a larger and more dedicated following. It also caused the extended play to reach a new peak of No. 6.

Squeaky became an administrator for Flex Entertainment on June 29, 2020, after administrator Yung Garfield left the label; however, Garfield re-signed to the label on July 3 and would become an administrator again alongside Squeaky.

Squeaky announced in June that he changed the title of his second studio album to God Mode.  The album’s lead single “Rollercoaster” was released on July 3, 2020 and peaked at number 28 on the Flex Entertainment Hot 100. On that same day, Squeaky appeared on three songs on the Flex Gang, vol. 2 compilation album: His own songs, “Moonshine” featuring Lil Toy Yoda and Lil Joof, and “Nipples 2” featuring Big Baller B, Lil Mosquito Disease, Lil Toy Yoda, Lil Joof, and Yung Lambo; and as a featured artist on Yung Garfield’s song “New Beans” featuring Lil Squeaky and John. On the Hot 100, Moonshine peaked at number 24 and New Beans at 27.

Squeaky released his second studio album God Mode on July 24, 2020. The album was met with very positive reviews, becoming the highest rated Flex Entertainment album on the album reviewing site AlbumOfTheYear at the time. Many listeners and critics praised the more polished sound and improved mixing and mastering, as well as Squeaky's infectious flows and vocal performances and often funny lyrics. Some critics disliked some of the lyrics and mixing, but the majority of listeners gave the album very positive feedback. The album's reputation has improved over time, with many considering it a classic in Squeaky's discography and in the Flex Entertainment catalog. Its sound has recently been described as a hybrid between outsider hip hop and melodic trap. The album debuted at No. 3 on the Braeden's Most Played Songs chart with 220,000 units sold. Numerous songs off the album have surpassed 1,000 plays on Spotify, with the most popular song, "Crocs on my Feet," spawning a TikTok challenge in which people show off their diamond-plated and designer Crocs shoes while the song plays in the background.

Squeaky released a number of non-album singles in the latter half of 2020, including "Blockbuster" featuring Young Seagull, "Menace 3," the highly anticipated sequel to Menace and Menace 2, and "Molestor Moon" with Lil Mosquito Disease, Yung Lambo, Yung Garfield, .jitters, Cedric, and Lil Nav. He then announced his fourth mixtape, and his first since Jews in the Ghetto, vol. 2, Squeaky 4 President 2: The Re-Election. The mixtape was preceded by the lead single, "Squeaky Claus," which was a Christmas song. The song was met with very negative reception, with many fans wondering where the Lil Squeaky they knew and loved from God Mode went; the song did grow in reputation and popularity during the 2021 holiday season. Squeaky 4 President 2 was released on December 4, 2020, and was met with mixed reviews upon release. Many listeners and critics stated that while the album was fun to listen to, the majority of the songs were rather forgettable, and not nearly as enjoyable as the more focused material found on God Mode. The mixtape debuted at No. 4 on the Braeden's Most Played Songs chart with 150,000 units sold. Since its release, however, the mixtape's reception has vastly improved, with many fans regarding it as a sleeper hit and one Squeaky's better projects.

Squeaky has worked on other Flex artists' albums as well, starting with his role as "creative director" of Yung Garfield's debut album BOMBOCLAAT. Squeaky helped out a lot with samples and telling Garfield what to do for a certain song's production or lyrical topic. He also taught Garfield how to "produce in Audacity," a style of production that Garfield has stuck to ever since and has brought him great success. In addition, Squeaky was the sound engineer for Yung Lambo's debut album Lambo Season. He was also featured on multiple songs on each of these albums. He has featured on many large collaboration songs with several artists including "MOLESTER MOON" and "Side Effects Remix".

Lil Squeaky stepped down as exec on February 23, 2021. He stated the position brought a lot of unexpected stress, and he wanted to return to treating Flex more casually and distantly like he had done before becoming admin or exec. He also felt that he had become somewhat "addicted" to Flex, and taking breaks and leaving the server didn't help much, so leaving his position of power he felt was the best move to relieve his stress.

Squeaky has also announced a multi-genre album, initially titled FAIR LAKES PLAZA. The working title was then changed to Squeaky, and then to Fever Dreams, and then to Purity, before Squeaky announced that the album had no title. In February 2021, he formally announced the album, titled In Development, set to release on March 26, 2021. The album's tracklist was revealed on March 19.

On March 26, Squeaky released his third studio album In Development with features from Young Seagull, 2Maajor, Kid Floral, Lil Mosquito Disease, Lil Flexer and White Fury. The album was met with varied reception with some saying it was the best Flex Entertainment release ever with its more "serious" sounding approach, focused lyrical themes, and genre experimentation, while others criticized it for its more serious approach and subject matters which came across as corny to some, and many consider it one of Squeaky's most polarizing releases. The album debuted at No. 1 on the Braeden's Most Played Songs chart with 360,000 units sold. He dropped another single "The Years Untouched" a few weeks after the album, featuring production from Shrekneck and the late Cedric. The single featured deep inspirational lyrics about how DJ Khaled taught Lil Squeaky to always win and take Ws.

Squeaky left the label in April 2021, keeping his reasons for leaving mostly ambiguous. After leaving he joined the small label and boy band juicyFlail, a decision met with much scrutiny by Flex members. In this new group, Squeaky released the triple-single Spooky Hours 2, a sequel to his Spooky Hours double-single from 2019. The tracks were originally intended to appear on the mixtape JEWS IN THE GHETTO, VOL. 3, which ended up being postponed indefinitely. The triple-single was met with mixed to negative reception, with listeners calling the songs boring and generic, and featuring none of Squeaky's typical energy or passion. The triple-single was so hated by some that observers and fans predicted that Squeaky might fall off soon.

Squeaky would go on to release the single "BITCHES ON ME," featuring Lil $teeve, Lil Quick & his old persona XXX Biggie T, in June. The single was met with negative reception as it came across as "trying too hard" by many of his hardcore fans. The song would later be considered a flop and was no longer praised. Squeaky released two more singles soon after: "CHECK" featuring Lil Mosquito Disease, and "WAY2GO" featuring CRZFawkz, both of which were well-received by fans and helped restore Squeaky's good will.

Amidst the releases of these singles, Squeaky announced his fourth studio album SITUATION, initially slated for release on July 23, 2021, a year after God Mode. However, Squeaky failed to release the album on that day, saying it wasn't done yet. This was actually the 2nd time Lil Squeaky and Kanye West had slated albums for release on the same day, with God Mode coming out on the day that West's album Donda: With Child was supposed to release, and both SITUATION and Donda not releasing on July 23, 2021. SITUATION released on September 3, 2021, to generally mixed reception with some fans seeing it as a return to form after the polarizing In Development and others seeing it as a step back. The album saw Squeaky drawing heavy influence from Memphis phonk music and underground hip-hop, as well as other styles like pop-punk and cloud rap. The album's production and energy were praised however it was criticized for its length, feature choices and lack of variety musically. The album debuted at No. 5 on the Braeden's Most Played Songs chart with 200,000 units sold.

Squeaky in dropped two more EPs in the remainder of 2021. The first was "NARCISSIST / Kanye Pooh" which was a speed-run mixtape that was met with harsh reception from fans and critics alike. The EP debuted at No. 34 on the Braeden's Most Played Songs chart with 80,000 units sold. The second was "Days Before Menace 2 Society" which was a compilation EP of old Squeaky leaks released onto Spotify including infamous tracks like "Hurt You" and "Adlibs (Interude)". The compilation EP failed to chart. Squeaky also twice attempted to release his leaked Menace 2 Society compilation onto streaming services with extra unreleased tracks, but it was rejected by Distrokid both times, first for the sample on "Mambo No. 69," and again for the inappropriate title of "Never Really Happened (Holocaust)". An instrumental song titled "My Happy Song" was uploaded to Squeaky's Spotify page around this time, and to this date nobody knows how it got there or who uploaded it.

Lil Squeaky signed back to Flex Entertainment in January 2022 to the surprise of many, with no prior announcement. On January 15, Squeaky released his comeback in the form of a double single titled "THE RETURN / PETER PAN." The double single was met with generally positive reception, with a lot of people praising THE RETURN for being a return to form from the rushed NARCISSIST / Kanye Pooh EP. Squeaky announced another single, "Undercover" featuring Thick & Thin, which was rejected by Distrokid for its copyrighted cover art. Instead of releasing it on the intended release date, however, Squeaky surprise-dropped the long-awaited "Menace 5," featuring Lil Mosquito Disease, Tending Bike, and Lil Stuart Little. The song and its music video were released on January 21 to positive reception. "Menace 5" became his highest charting song on the Flex Entertainment Hot 100, peaking at number 2. Shortly after, he announced his fifth mixtape The Sex Tape, set to release in early 2022. He released "UNDERCOVER" featuring Thick & Thin, on January 28, which peaked at number 6.

On February 5, Lil Squeaky released not one, but two mixtapes. The Sex Tape and the Scary Mixtape, the latter of which was dropped a few hours after the the first. The Sex Tape was met with mostly positive reception (with the exception of the well-known police officer Yung Lambo and mass murderer "Jackson" who told Squeaky to make rage songs then didn't like the tape) as many praised the tape for going back to a more fun sounding and energetic Lil Squeaky, as well as praising the rage influence and feature performances from Tending Bike, Voda Wake and Lil Mosquito Disease. The mixtape debuted at No. 3 on the Braeden's Most Played Songs chart with 270,000 units sold. The Scary Mixtape had more varied mixtape as many were "too scared" after listening to it. The mixtape debuted at No. 13 on the Braeden's Most Played Songs chart with 160,000 units sold. Soon after the release of these projects, Squeaky went to Twitter to state that his next project would be his "most based, artsy, introspective, and positive one yet". Squeaky announced in March that his new album would be titled Art, set to release sometime in the spring, and he proclaimed the album would be the "most positive album in the history of Flex Entertainment and the internet rap scene," telling fans to "prepare to embrace the based philosophy." The lead single "Only One" featuring Hood Guy was released on March 18. The album was announced for an April 15 release.

Squeaky took to Twitter in February 2022 to state that making EPs was stupid; shortly after, he announced a new EP called Based 1, which was released on February 18. The EP received praise for its experimental style and influence from abstract hip hop, as well as its based energy. As with many EPs, it failed to chart. Shortly after, Squeaky released a controversial promo video called "$TUNNIN," which confused many, and seemed to take shots at Payden McKnight with its description reading "102.3 IS NOW," a clear reference to Payden's previous rollout themed "101.2 IS NOW". Later, this promotional tactic was revealed to be a part of the rollout for Squeaky's collab album with Payden, McDonald's. The two released a 2-part EP titled Days Before McDonalds to build hype for the project. The EP debuted at No. 31 on the Braeden's Most Played Songs chart with 80,000 units sold. Squeaky has also spoken about making a "rock album" with influence from Machine Gun Kelly, in response to demands from fans for him to quit trap music and become a rock artist. The album was quietly cancelled, but Squeaky has stated that he will release the finished tracks in the near future.

Art was ultimately released on April 15, 2022, and was met with widespread praise from listeners, many of whom proclaimed the album to be a return to form for Squeaky after a period of lackluster releases. The album was praised for its diverse production, Squeaky's performances and personality across the album, the strong and heavily integrated feature verses, and the emotional strength of the album, including the highly positive "based" messages throughout the album. The album immediately became regarded as one of Squeaky's strongest releases, being called a "victory lap" by famous music reviewer and professional computer user TheDankestMeme. More importantly, Art helped restore Squeaky's good will in the label, and brought back many older fans who disliked or refused to listen to his newer output. The album debuted at No. 3 on the Braeden's Most Played Songs chart with 220,000 units sold. All twelve tracks on the album charted within the top 40; however, most songs failed to achieve staying power as singles due to their long length and production style. Despite this, the lead single "Only One" rebounded in popularity after the album's release and reached the top 10 for the first time, peaking at number 6 thus far. The album track "Darkness" featuring Beetlebat proved highly successful and was later released as a single, gradually gaining traction as a sleeper hit; the song has thus far peaked at number 10.

Following the success of Art, Squeaky began producing for several other artists and recording several feature verses for other artists. His next single was the Lil Cox joint track "Who Da F?ck Is Pillsbury DoughBoy"; though the song debuted in the top 20, it ultimately underperformed, partially due to releasing randomly on a Sunday. Squeaky's next single, "One Bent Knee" featuring Beetlebat, was far more successful and well-received, with many praising the 90s pop-R&B style and the song's strength as a single. Lil Squeaky has not stated if either of these singles are for a project. Squeaky also hinted at transitioning to pop rap in the near future, particularly after the warm reception of One Bent Knee. Squeaky's next single release was "What Happened" featuring Kenny Mgee, released on June 24. The song, which took heavy influence from indie pop, was generally well received and is currently the subject of several playlisting strategies by Squeaky. Around this same time, Hood Guy performed a publicity stunt on Twitter in which he replied to every tweet he saw with a clip of his verse in the Only One music video, which had released on the same day as One Bent Knee. This stunt, in conjunction with the clip accumulating many views on TikTok, resulted in the music video for Only One gaining many more views, becoming the third time the song rebounded in popularity. Hood Guy attempted another publicity stunt by taking to SoundCloud to repeatedly state that he carried Squeaky on the song.

In late spring of 2022, Squeaky began the rollout for his next project which at the time was titled "Based Rockstar". The project was stated to be very punk inspired and there were several songs created for it before Squeaky would eventually cease work on it due to struggling to make an entire album using punk instrumentals. Squeaky's most recent compilation of scrapped songs, Months After Menace 2 Society, contained several of the finished punk songs, such as "Punk" featuring Beetlebat, "Diamonds" featuring CRZFawkz, and "Based Rockstar." The scrapping of the pop punk album would lead to the creation of his sixth studio album It's Just Different which would be a pop album. Prior to its release, Squeaky had begun to tease the release of numerous pop songs billed as "fun summer bangers," with the singles "One Bent Knee" and "What Happened?" being far more pop-oriented than previous Squeaky releases. It's Just Different was announced the week before it came out, and the album was released on July 22 to extremely positive reception as fans called it catchy, consistent and very unique for Squeaky's career. The songs across the album received significantly higher streaming numbers over their first weekend than songs from other Squeaky albums would, with some predicting that It's Just Different will be Squeaky's most successful album.

Political Career
Lil Squeaky was elected to the Flexistan House of Representatives in 2014, representing Virginia's 8th congressional district based in Alexandria. Prior to entering the race, he founded the Baller Party, and would go on to be the first and only member of Flexistan's Congress to be a member of the Baller Party, though it is rumored that Wisconsin Senator Big Baller B will switch to the Baller Party at some point. Squeaky's narrow victory in the race against professional scammer and Gay Party nominee Lil Boy was widely attributed to the endorsement he received from popular political commentator $nipa Dolla.

Squeaky was re-elected in 2016 and 2018, and declined to seek re-election in 2020 as he sought the presidency of Flexistan. He promoted his presidential bid with the Squeaky 4 President EP. He received the Baller Party nomination uncontested; however, he received only 0.69% of the popular vote in the general election. Squeaky called the election rigged, and released the Squeaky 4 President 2: The Re-Election mixtape, in which he claimed that he won the election. Upon the inauguration of president Yung Lambo of the Tyrant Party in 2021, Squeaky announced he would forcefully seek the presidency in 2021, and created a fake election in November in which he pretended to be elected president in order to confuse the media. Squeaky called himself a "rockstar" and a "punk rapper" in his fake victory speech; however, he later conceded the 2020 election and admitted he was not the president, and announced that he would run for his old House seat against the incumbent, Socialist Party politician Lil Pinecone. Polls show Squeaky beating Lil Pinecone by a 90% margin.

As a member of the Flexistan Congress, Squeaky was known as a vocal opponent of former president Yung Tegga, and advocated for reinstating former president Lil Flexer as the president. Squeaky also made many bold statements, such as stating that all politicians should switch to the Baller Party, that Gay Party politician Yung Garfield "fell off," and for ghostwriting an offensive lyric for a Yung Garfield album dissing Socialist Party politician Lil Toy Yoda, that said "Fuck Lil Toy Yoda, I'm not mastering your album"; Squeaky also stated on a Yung Garfield song that he is a "clout chaser like Lil Toy Yoda." He also called Kansas Senator Yung Schmoobin "El Crapo Jr.", due to Schmoobin's ties to Mexican drug cartels, and called California Governor Lil Mosquito Disease a "dictator" and a "supreme leader." Squeaky has repeatedly spoken out against the "Flexistan establishment," and has advocated for a "Punk Revolution to occur Now".

Lil Squeaky has stated that he will be running for president in 2024, and declared his intention to run in the 2024 race back in 2014 when running for Congress.

Artistry
Lil Squeaky has described himself as a "punk rapper" and a "rockstar," due to his frequent release schedule and disregard for norms, albums rollouts, promotional tactics, and trends; rather, Squeaky has stated he prefers to "roll himself out as an artist." Squeaky is known for his use of altered samples and melody loops in his production; in his earlier beats he used the samples and loops almost unaltered, whereas in more recent beats he has typically altered the samples heavily with many distortion, bitcrushing, phase, and reverse effects. Squeaky's music is known for its replayability and ethereal nature, and he is often considered a cloud rap artist. Most of his music is trap rap, though he has experimented with other genres like R&B, pop punk, bedroom pop, boom-bap, and indie rock. Squeaky's lyrics typically focus on flexing, sex with women, material objects such as cars, and various references to video games and movies. More recent releases feature lyrical topics regarding positivity, nature, love, and partaking in day-to-day activities.

Many aspects of Squeaky's music have been described as "outsiderish," or resembling outsider hip-hop. For example, the simple and repetitive sampling, unaltered royalty-free melody loops, alternating hihat samples, and hazy sound of God Mode are praised by many fans, and are likened to outsider hip-hop from artists like Viper and Lil B. More recent releases such as The Sex Tape see a return to the very repetitive and hazy samples and melody loops, and see Squeaky utilizing very aimless and questionable lyrics, also likened to outsider hip-hop. Squeaky also dabbled in numerous genres that were more singing-intensive on In Development, such as pop, alternative, and R&B, and took heavy inspiration from old-school Memphis trap and phonk music on SITUATION. Most recently, he has taken heavy influence from artists like Lil B, as well as old-school hip-hop, cloud rap, and more abstract hip-hop on Art.  Squeaky has hinted at a pop-punk or rap-rock transition on a future project, as well as a transition into pop rap.

Fan Reception
Squeaky was one of the most praised Flex Entertainment members for a long time, with God Mode being considered a staple of the Flex catalog for a very long time. In 2020 he was one of the most highly requested feature artists in the label; his praise increased when Big Baller B placed God Mode in his Top 10 Albums of 2020. Upon leaving the label in 2021, Squeaky's reputation and level of praise sharply decreased, with former fans sending much more criticism towards him. Former Squeaky stan Yung Lambo has heavily reversed his past praise of Squeaky, saying much of his music was never even that good. Fellow former Squeaky stan CRZFawkz has decreased his liking of most Squeaky projects as well and no longer considers many of Squeaky's songs to be top Flex songs. Upon returning to the label in 2022, however, Squeaky acquired a new generation of fans who discovered him through comeback singles like "The Return" and "Menace 5," as well as the Based 1 EP. His frequent collaborations with rapper Lil Stuart Little have also helped him gain new fans, as Lil Stuart Little's popularity exploded in early 2022. In addition to these newer fans, Squeaky gained listeners from the underground in the later months of 2021 thanks to the old-school Memphis-inspired sound of his SITUATION album. Recently he finally began to receive similar praise to what he used to after the release of Art, which many have called his best project thus far, and his pop album It's Just Different was much more well-received than expected.

Controversies
Lil Squeaky has been considered one of the most controversial artists in Flex Entertainment, due to his sense of style and "mid" music.

Throughout 2018, Lil Squeaky was in a short lived rap beef with rapper "Lil Crisp" better known by his real name Bivash which resulted in the song "Fake Lil Squeaky". The rap beef was revisited in late 2020 once various Flex Entertainment artists found out about it.

In late 2020, Squeaky generated backlash from members of his label when he began to repeatedly shout out Trap Lore Records, a label founded by YouTuber Trap Lore Ross. Many members of Flex began to fear that Squeaky would leave Flex to join Trap Lore Records, claims which Squeaky doubled down on by saying he would. This led to executive Yung Garfield enacting a strict ban on mentioning Trap Lore Records.

The following winter, Squeaky entered a beef with Yung Garfield, after Squeaky opposed Yung Garfield becoming an executive again immediately after signing back. Squeaky also dissed Garfield by saying he fell off. This resulted in Garfield having a meltdown in Flex's discord server and calling Lil Squeaky a bitch, before leaving the label and server. When Garfield signed back several months later, he immediately became an executive again.

People have accused Lil Squeaky of being a racist, despite him having made a song called "Fuck Racist" in which he disses racists.

Squeaky's youngest brother Lil Nav is infamous for being a professional scammer, who frequently studies scam tactics by listening to songs by American rapper, hacker, and scammer Teejayx6. Lil Nav utilized profits from his only song, "Extreme Gungeon Terrors Nanana," part of the 2021 Flex Fridays series, to fund his illegal ventures, such as an attempt to negotiate a treaty with Belgium to annex Cuba under the Flex Entertainment Empire. After Squeaky condemned Lil Nav's illegal actions, Lil Nav cried about it and called Squeaky a "snitch" and a "cyberbully," the latter insult being the thesis for Squeaky's hit song "CYBERBULLY" featuring WT, the most popular song off of his SITUATION album. Squeaky has sported a variety of hairstyles during his time in Flex, many of which have been the subject of scrutiny. Upon joining, he sported a short forwards quiff hairstyle, which many described as looking like a sponge or a paintbrush. In 2020, he grew his hair out longer, adopted a medium-length sideswept look. He donned blonde highlights in the spring of 2020, which he was teased for by some. In summer, he cut his hair short again, sporting a side-parted quiff hairstyle that was mostly received favorably. In December 2020, a selfie he took after receiving a haircut went viral, with many stating that his hairline looked messed up and that he looked like an egg. His unstyled hair has been compared to that of Canadian rapper Nav. Similarly, Squeaky's fashion sense has been teased by some, as he tends to wear smart casual to formal clothing. In spring and summer 2020, he very frequently wore floral shirts, which were complimented by some and scrutinized by others. His overcoats and assortment of jackets have suffered similar fates, most notably an infamous picture of Squeaky wearing a blue and white flower-patterned suit for his senior prom.

Lil Squeaky has also been accused of ripping off famous rapper and stripper Alpha M's drip. Squeaky has embraced the accusation stating that Alpha M has inspired him to make songs about putting the bungus in the chungus.

Lil Squeaky entered a feud with Flex Entertainment executive Yung Lambo for releasing too much music in early 2022, as they stated that uploading all of his new releases, particularly his compilation albums, to the Flex Entertainment Youtube channel would overshadow smaller artists and decrease viewer engagement. Squeaky's compilations were ultimately uploaded to the Flex channel, causing his songs to occupy over 50 spots on the Flex Entertainment Hot 100 at the same time in February 2022. Squeaky dropped a diss track on Yung Lambo which was a parody of "Super Gremlin" by Kodak Black, which was widely praised, and caused many to begin calling Lambo "the gremlin." Lambo responded with a diss track remixing "Imma Dogg" by NLE Choppa, which everybody hated, causing even more people to call Yung Lambo "the gremlin."

Lil Squeaky scared many people with the scary mixtape.

Trivia

 * Lil Squeaky's verse on his song "XEXE" is potentially the fastest verse ever rapped by a Flex Entertainment artist.
 * He moved to Finland in August 2021 for college, where he is studying Electrical Engineering and minoring in Computer Science.
 * Many of Squeaky's older songs on Soundcloud have been recently gaining traction and have become sleeper hits. Some notable examples are "MANNY", "Oolin", "XEXE", "Arms Race", "Cclapped" and most notably "b r o k e n h e a r t e d" which even received a remix in September 2020 with popular Flex Entertainment artist Big Baller B.
 * His older SoundCloud projects have also gained traction in recent years, most notably "Professional Murderer" and "SQUEAKERTON: The Chronicle".
 * He knows Flex Entertainment artist Lil Pinecone and former Flex Entertainment artist Lil Boy in person, having met them through his brother and former Flex artist .jitters.
 * Squeaky, .jitters, and Lil Boy all starred in a production of the musical Anastasia at Squeaky and .jitters' high school in July and August 2021, with Squeaky playing the main villain role of Gleb Vaganov.
 * He had the most XP in the Flex Entertainment Discord Server for a very long time before being surpassed by Yung Lambo.
 * He is one of 2 Flex Entertainment members to have released a live album, the other being CRZFawkz.
 * He is one of two Flex Entertainment artists to have an entire "project" of theirs leaked with the compilation "Menace 2 Society" being leaked by allegedly Fastoosh Kaloosh on FLEX LEAKS. The other artist to have had a project leaked is Lil Toy Yoda.
 * Lil Squeaky has two song trilogies as of 2021. The Menace trilogy and the Nipples trilogy.
 * Lil Squeaky is well known for being a "creative director" or executive producer for various Flex artists' projects. Well known examples include his work on BOMBOCLAAT and Lambo Season.
 * Squeaky is well known for his Discord profile pictures which often remain the same for entire months, the most notable being Avatar James Charles, 6ix9ine, Offred from The Handmaid's Tale, DaBaby, Barney, Rod Wave, A$AP Rocky, Rick Ross, Dobby and currently NAV.
 * Squeaky finally achieved a #1 song on the Flex Hot 100 on July 29th, 2022, with the hit single "One Bent Knee" featuring Beetlebat after the release of "It's Just Different."